Insight into Structure-Function Relationships and Inhibition of the Fatty Acyl-AMP Ligase (FadD32) Orthologs from Mycobacteria

J Biol Chem. 2016 Apr 8;291(15):7973-89. doi: 10.1074/jbc.M115.712612. Epub 2016 Feb 21.

Abstract

Mycolic acids are essential components of the mycobacterial cell envelope, and their biosynthetic pathway is one of the targets of first-line antituberculous drugs. This pathway contains a number of potential targets, including some that have been identified only recently and have yet to be explored. One such target, FadD32, is required for activation of the long meromycolic chain and is essential for mycobacterial growth. We report here an in-depth biochemical, biophysical, and structural characterization of four FadD32 orthologs, including the very homologous enzymes fromMycobacterium tuberculosisandMycobacterium marinum Determination of the structures of two complexes with alkyl adenylate inhibitors has provided direct information, with unprecedented detail, about the active site of the enzyme and the associated hydrophobic tunnel, shedding new light on structure-function relationships and inhibition mechanisms by alkyl adenylates and diarylated coumarins. This work should pave the way for the rational design of inhibitors of FadD32, a highly promising drug target.

Keywords: crystal structure; drug design; enzyme inhibitor; fatty acyl ACP-synthase; fatty acyl-AMP ligase; mycobacteria; tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Antitubercular Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / chemistry*
  • Bacterial Proteins / metabolism*
  • Carbon-Sulfur Ligases
  • Crystallography, X-Ray
  • Drug Design*
  • Ligases / antagonists & inhibitors
  • Ligases / chemistry*
  • Ligases / metabolism*
  • Models, Molecular
  • Molecular Sequence Data
  • Mycobacterium / chemistry
  • Mycobacterium / drug effects
  • Mycobacterium / enzymology*
  • Mycobacterium Infections / drug therapy
  • Mycobacterium Infections / microbiology
  • Mycobacterium tuberculosis / chemistry
  • Mycobacterium tuberculosis / drug effects
  • Mycobacterium tuberculosis / enzymology*
  • Mycolic Acids / metabolism
  • Protein Conformation
  • Tuberculosis / drug therapy
  • Tuberculosis / microbiology

Substances

  • Antitubercular Agents
  • Bacterial Proteins
  • Mycolic Acids
  • Ligases
  • Carbon-Sulfur Ligases
  • long-chain-fatty-acid-(acyl-carrier-protein) ligase

Associated data

  • PDB/1ULT
  • PDB/3KXW
  • PDB/3R44
  • PDB/4IR7
  • PDB/5EY8